Nathan Sykes

April 30, 2021

Howdy Interactive is hiring a Chief of Staff

My firm, Howdy Interactive, is hiring a Chief of Staff to work with me as I begin my college career.

Above all, I'm looking for a bright, intelligent, motivated young person to take this position. I prioritize work ethic and an eagerness to learn over people with lots of textbook experience, but you must have a fundamental understanding of corporate finance to be effective in this role.

The fun stuff - the base salary for this position is $125,000 USD. Bonuses are based on the performance of our rolling fund, but should equal about 75% of your base. Reasonable benefits. This is a permanent, full-time position. You must be willing to relocate to Connecticut, and travel with me quite often (25% of the year). Shadowing me and my day to day work is extraordinarily important for this role.

Let me be clear - you'll earn more money at 50% of companies, even when you factor in your bonus. If a paycheck is all you're after, then go apply somewhere else.

We do our damn best to do business differently at Howdy. We'll fire you if you work 75 hour weeks - 40 hours is more than enough to get the work we need done. We're not changing the world, we're just doing business. What can't be finished at 5pm on a Friday can be picked up at 9am on Monday (while realizing that the occasional after-hours engagement is just the cost of doing business). If you're a workaholic that can only see themselves doing 12 hour workdays, you won't thrive here. It's perfectly clear to me that if we put more hours in, we could scale faster - we're making the conscious decision to take an alternate route. Our team, both in our head office and the staff that operate our portfolio companies, is entirely remote (the only reason you won't be is because I need you on-site with me to be fully effective). The emptier our offices in Connecticut - the better. We want the best staff for the job, not just the staff in the local area.

About The Job

I'm hiring a Chief of Staff to act as my eyes and ears as I begin my academic career at a college known for its rigorous and thorough workload. For the last four or five years, I've run Howdy Interactive, which has taken on many forms - first as a marketing firm, now doing investment work in the private equity field. We buy, start, manage, and hold super small, super simple companies doing $500,000/yr or less in net profit.

I'm looking for someone to shadow me in my day-to-day work, and start to save me time, energy, mental bandwith, and money. That might take many forms, such as:

  • Conducting initial due diligence meetings with companies looking to sell their business to us
  • Making sure the systems we use to conduct business don't break under increasing pressure
  • Deal with issues before they come up, like if a payment processor goes down temporarily
  • Recognizing that we could use a better service to achieve something, and preemptively reach out and get information on my behalf
  • Become a sounding board as we validate and look at new ideas for future micro-companies
  • Create partnerships with private lenders we can use for future LBOs, before we need their money

These are just a few examples. Once you spend some time seeing our company work, you'll be able to identify what exactly needs fixing. Then, fix that. Keep doing that until we can buy a private plane or a yacht or something stupid that rich people normally buy.

If this sounds like something you'd be interested in, email me your resume and the title of your favorite book. I can be reached at

- Nate Sykes